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How to Stop Being Awkward with Older Women in 10 Steps

awkward man with older women

Many guys want to start dating above their age but need to figure out how to stop being awkward with older women.

They aren't use to their confidence, sophistication, and how they take far less bullshit.

Older women can offer you amazing experiences and teach you a great deal about life, sex, values, relationships, and more.

But, it's extremely important that you’re comfortable in your own skin and can show her that even though you're younger than her, that you're a MAN and not a boy.

How to Stop Being Awkward with Older Women

If you want to know how to stop being socially awkward with women, follow these 10 steps:

#1: Accept that she might be more experienced than you in life

As a man, a lot of times you'll find that you have more experience than the girls you're dating — whether in sex, relationships, or life in general.

However, with older women it might be the complete opposite.

She might know more about orgasms.

She might have had several long-term relationships.

She may have even travelled to 30+ countries and started several businesses.

Don't be surprised if this is the case.

You might feel emasculated because she’s more established and has experienced more of life than you have. Don't let this be a reason to be insecure.

But remember: Of course it makes sense that she's experienced more than you!

She's lived 10,15,20+ years longer!

Don't just let what you've done or what you have be the measure of your masculinity and character.

If she wants to talk to you, she likes you – Not your business, not the number of passport stamps you have, not your black book... but you.

Be OK with not knowing as much as her and, maybe, she'll be glad to teach you a thing or two ;).

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#2: Accept that she's probably much more comfortable with herself and her sexuality

As we go through life, we learn to accept that we'll always have some flaws and anxieties that annoy us.

We have some strengths, and some weaknesses, and that's OK.

We're still good people who can kick some ass.

We become more comfortable in our skin and chisel out the belief that, “If they don't like me, too bad! I like me and I'll go find other people who like me too.”

An older woman has 10+ years on you in getting this carved into her belief system, so don't be surprised if she's very comfortable with herself.

She might not waver on discussion points and she'll defend her views enthusiastically.

She'll be very passionate about what she likes and if you make fun of her she'll get upset.

She also might be VERY open with her sexuality — in terms of what she likes and doesn't like, and even overtly staring you up and down.

All this comes from her sense of security and being happy with herself.

You can be intimidated by this, or turned on by her confidence.

#3: Set relationship expectations early and be OK with saying “no” to being the provider

The older women you're dating may be divorced or have families and children from previous relationships.

You need to be comfortable with this possibility.

Even if they don’t have children yet, women are on a biological clock when it comes to safely giving birth and we know that a woman's looks do decline rapidly with age as opposed to a man's.

In other words, the older women you’re dating may be looking for someone to take care of them or to start a family as soon as possible.

While some older women will be happy to just have fun with you, some will be looking for you to fill the role of “boyfriend/provider”.

If you aren't looking to fill this role with her and it's not something you want, be sure to be up front with her and let her know. This is a great attitude that many "nice guys" lack.

It doesn't mean that you don't care about her family or her desire for a long-term relationship and family life.

Make sure she knows that you accept those parts of her, but that you aren't interested in being that guy.

There's nothing wrong with setting boundaries, and she'll appreciate your honesty because of point #4...

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#4: Want to know how to stop being awkward with older women? Stop playing “the game”

If I text X and she texts Y, what should I do? How long should I wait? Can I be forward? How do I ask her to come home with me?

A lot of “the game” comes from being scared to be up front with your intentions, and thinking you need to have some sort of complicated sequence to unlock the “magic vagina” of a girl.

This all might seem normal when you’re dealing with a college girl. But to an older woman it's just sad and confusing.

Older women know what's up.

They've most likely dated around — they've seen the tricks and lines and all that.

Girls are known to be socially tuned in and aware.

But older women will take it to another level.

Learning how to stop being awkward with older women means you need to drop the phony acts and lines.

They might work on girls in the 18 to mid-20s age range but it's not going to work on older women.

She's going to think, “Wow, this guy needs lines and all that BS to feel confident? Screw this, I'll find someone else.”

She has even less time to waste and has the experience to know what she likes and doesn’t like.

Save yourself some needless rejection and just be up front and honest with her.

And since she doesn't play the game, here's something else:

#5: Learn how to communicate authentically and honestly

Many guys are very bad at handling and expressing their honest emotions and thoughts.

In fact, that's what screws a lot of us up from succeeding with women (see: Mark Manson's work).

On average though, older women will be more open and up front about what they think and how they feel.

If she likes you, she'll tell you.

If she thinks you're being needy, she'll tell you.

Again: she's tired of “playing the game”.

She wants someone up front and straight forward she can enjoy her time with.

Start becoming comfortable having authentic and honest conversations with women, your friends, and everyone around you.

This will make you much more attractive.

Sure, being super up front might scare off the girls you have to “game.”

These are the girls who get uncomfortable with you telling them that they're beautiful right when you walk up to them.

The girls who need to make fun of you for some reason right after to defuse the situation...

But if a girl requires a bunch of backhanded techniques and indirect tactics to date, isn't that a lot of work for no reason?

Is that really the type of girl you want to be around?

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#6: Don't assume you can just “Netflix and Chill” on the first date

Inviting a girl directly to your place under the pretense of watching a movie might work in college and in some cases with certain older women. This type of attitude may be the reason girls don't like you.

But you’ll most likely be expected to take her on a *gasp* REAL DATE.

Note: REAL doesn't mean EXPENSIVE.

Don't spring for $200 dinners if you think you need to do it to get her approval or that she'll magically sleep with you because of it.

Don't just do it because you think you need to show her that you have money.

That will just backfire.

You can just go for some simple drinks at a bar.

But older women are most likely going to expect you to take them out somewhere before bringing them home.

Oh, no.

You have to have an actual conversation and get to know a potentially awesome woman.

How tragic!

#7: Don't endlessly text and bother her: She's going to be independent and expect you to be too

Older women have their own lives, much more so than younger women.

Men are used to being more independent and while she'll probably still text you, over texting and trying to engage with her in tons of conversation throughout the day is going to make it appear like you have no life. And come off as very needy.

You should absolutely text her and enjoy her: that's what dating is all about.

But don't get weirded out when you don't get texts from her all the time — that's just more validation you're looking for to make your ego feel better.

She likes you, she's just off doing her own stuff.

Text her a bit later, get her over, and then her attention will be all on you and not her day ;).

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#8: Expect faster rejections: Older women know what they want and what they don't

A younger woman will put up with more insecurity and neediness in you because she's still working out her own and is, on average, less established than an older woman.

On the other hand, older women know that time is the most valuable resource they have.

They've been through several relationships, one night stands, hook-ups, and life experiences.

They know what they want and if they don't see it in you, they'll move on much faster.

That doesn't mean that they'll be mean or harsh or anything.

They may just simply tell you that they aren't interested even after a minute of talking to you.

If she takes a pass on you, accept that older women have refined tastes and improve yourself so you'll catch the eye of the next one that you come across during your day.

#9: Be prepared for the fact that older women will probably have more baggage

Nobody gets through life unscathed.

The more you live, the more you experience... both good and bad.

For an older woman who is 15-20+ years older than you, she might have been through some harsh stuff — whether in relationships or otherwise.

As you continue your relationship together, even if it's very casual, her past might come up more so than a younger woman who hasn't experienced as much.

Just be prepared for it and accept that it's part of the territory.

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#10: Be mature

No sagging jeans off your ass.

No just getting by at McDonald's with no advancement plan.

No farting at the table.

This is a woman and she expects a MAN.

While she might be entertained by your youthful energy, it's not going to make her want to have sex with you if you're behaving like a teenager and dressing like one.

Older women are more refined, elegant, and sophisticated.

And while they don't necessarily expect you to own a corporation and dress in a tuxedo like James Bond, they will expect and be impressed by a certain level of maturity.

This means: dressing well, talking openly about your passions, being well travelled, and maybe knowing some different languages.

In other words, the definition of a well put-together man — which you should be working towards just for yourself!

Dating older women can give you awesome, rewarding, and fun experiences.

So if you want to learn how to stop being awkward with older women, remember these points about a woman you’re dating:

  • Accept that she might have more life experiences than you and baggage that might come up during your relationship.
  • Accept that she may be more comfortable in her own skin and with her sexuality.
  • Set relationship expectations early and honestly — tell her what you want and what she can expect.
  • Cut out the game bullshit.
  • Take her out on REAL dates — no “Netflix and chill”.
  • Have your own life — don't constantly text and bug her.
  • Be OK with getting quicker rejections when you don't meet her ideal of a man.
  • Make sure you work on making your communication open and honest.
  • Be mature.

Other than that, work on becoming comfortable in your own skin: your strong points, your imperfections, your mistakes, and what you love.

Older women (in fact ALL women) will want to be with you.

If you follow these suggestions and take care of these 10 steps, you'll be dating and enjoying older women in no time.


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